Boron tribromide → N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester

HRID 24642ノート

反応式

HRID 24642 の反応式
B(Br)(Br)Br.[CH3:5][O:6][C:7](=[O:35])[C@H:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33]C)=[CH:23][CH:22]=1)[NH:9][C:10](=[O:19])[C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:18]>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:35])[C@H:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])=[CH:23][CH:22]=1)[NH:9][C:10](=[O:19])[C:11]1[C:12]([Cl:18])=[CH:13][CH:14]=[CH:15][C:16]=1[Cl:17]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 54267959N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

生成物 1

HCID 54156646N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester収率 50.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

BBr3 (1 mL, 1M in CH2Cl2) was added to a CH2Cl2 (10 mL) solution of N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (0.215 g) at 0° C. with stirring and the solution was slowly warmed to room temperature. The mixture was stirred for 3 h and quenched with EtOH. The solvent was removed and the residue was taken up in EtOAc. The solution was washed with satd. NaHCO3 followed by brine, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1) to yield 0.105 g of N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester. ESMS: m/z 444 (MH+).

後処理

  1. stirringThe mixture was stirred for 3 h
  2. customquenched with EtOH
  3. customThe solvent was removed
  4. washThe solution was washed with satd
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1)

出典と根拠

ORDレコード
ord-b17fa2f91ee34ab6a7e9bb687d9790f5
出典データセット
uspto-grants-2005_02
特許番号
US06855843B2

反応ノート

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